Thanks for clarifying who you are, that would have been confusing. Different account and even different IP. Please try to be consistent with which account you use. While there are perfectly legitimate reasons for multiple accounts, they can also cast a great deal of suspicion upon yourself. Some misguided plugin and theme authors create multiple accounts so they can tell themselves how great their product is. Such behavior is not tolerated at all and it will not end well for them.
As I’ve no insight to why core devs do things, I can’t accurately answer. Going off my thought that it’s a method of convenience for situations where only one error can possibly occur, the first message happens to be the last message as well. So in that context they are showing the last message ??
The bottom line is if you need the last message of several, you are using the wrong method. You want WP_Error::get_error_messages() — the one with an extra S for the plural form of message.